Member-only story
Highway to Inferno: On the Road with the Oregon Proud Boys
Law-and-order rebels. Freedom-loving fascists. What makes the far right tick?

“My daddy served in the Army, where he lost his right eye
But he flew a flag out in our yard ‘till the day that he died”
Toby Keith’s daddy isn’t the only one. I’m idling on a sun-baked Oregon interstate just south of Portland, surrounded by lifted trucks carrying on the Keith tradition. The light summer breeze makes the countless flags dance in the shimmering heat. Trump 2020. Blue Lives Matter. American. Punisher. Gadsden. Confederate.
I don’t have flags myself, but Toby Keith at full volume with the windows rolled down seems like a decent substitute. After all, if you’re going undercover to provide live updates on a far-right event, it’s important to act the part.
The music is something more than tradecraft. Sure, I haven’t listened to “Courtesy of the Red, White and Blue” unironically for years. But I did listen to it sincerely at one time, and the truth is there’s part of me I can’t get rid of that loves this dumb song. I let myself sing along, words embedded in my brain from way back:
“And you’ll be sorry you messed with the U S of A,
We’ll put a boot in your ass, it’s the American way!”
Sometimes I miss the simplicity of words like these. I miss being young and stupid and brainwashed, waiting for high school to end and my 18th birthday to arrive so I could sign my enlistment papers and go fight for what I’d been told was freedom and democracy overseas. Flush my potential down the toilet to chase half-baked dreams of power and respect. I wasn’t much for country music at the time, but this song was a rare exception.
Maybe part of the reason I keep going to these far-right events is to relive that fantasy, just for a little while.

It’s September 7th — Labor Day — and I’m a single gas-burning cog in a long machine winding down the interstate: the Oregon for Trump 2020 Labor Day Cruise Rally. I’ve just spent the last couple hours wandering maskless…